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Ethyl bromoacetate → [5-(ethoxycarbonylmethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamate

HRID 344030
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HRID 344030 반응식
[C:1]1([N:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8](=[O:22])[O:9][CH2:10][CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[OH:21])[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:23]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:22])[O:9][CH2:10][CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:21][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:12]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
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참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 54103601(1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl N,N-diphenylcarbamate

생성물 1

HCID 70187804[5-(ethoxycarbonylmethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamate수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of (1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl N,N-diphenylcarbamate (67 mg), ethyl bromoacetate (33 mg) and potassium carbonate (37 mg) in N,N-dimethylformamide (1.0 ml) was stirred at room temperature for 5.5 hours and then extracted with ethyl acetate. The extract was washed with water and brine (twice), dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (toluene-ethyl acetate) over silica gel to afford [5-(ethoxycarbonylmethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamate (61 mg) as an oil.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine (twice),
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (toluene-ethyl acetate) over silica gel

출처 및 근거

ORD 기록
ord-b86df64f446d479ea2ac9539e8ba3f00
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05863918

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